Development of a carbon-carbon bond cleavage reaction is one of the important themes in synthetic organic chemistry. Particularly, the oxidative cleavage reaction of an olefin compound has been frequently used extensively. Conventionally, methods used frequently include a method in which sodium periodate is used as an oxidizing agent in the presence of a catalyst such as an osmium metal compound or a ruthenium metal compound, and a method in which ozone is used as an oxidizing agent (Non-Patent Documents 1 and 2). However, these methods have problems that, for example, the osmium metal compound is highly toxic, the ruthenium metal compound and the sodium periodate are expensive and produce a large amount of by-products during the reaction, the method in which ozone is used can potentially cause explosions, and furthermore, a large amount of power consumption is required for generating ozone. Thus, these methods cannot be said to be industrially suitable from the viewpoints of safety, cost, and environment.
Recently, therefore, a method for subjecting an olefin compound to oxidative cleavage in the presence of hydrogen peroxide has been attracting attention.
Patent Document 1 discloses a method for producing carboxylic acid, the method including reacting unsaturated triacylglycerol with hydrogen peroxide in the presence of a quaternary ammonium polybasic acid hydrogen salt and at least one selected from tungstic acid, heterotungstic acid, and their salts.
Furthermore, Patent Document 2 and Patent Document 3 each disclose a method for producing carboxylic acid, the methods of Patent Document 2 and Patent Document 3 being characterized by reacting an alicyclic alcohol oily solution with hydrogen peroxide and an alicyclic ketone oily solution with hydrogen peroxide, respectively, in a heterogeneous solution system in the presence of a catalyst containing a compound of a metal of Group 6 in the periodic table.
Hydrogen peroxide is safe and inexpensive. Furthermore, since it produces only water as a by-product after it is reacted, it is environmentally friendly. Thus, a method for subjecting olefin to oxidative cleavage using the hydrogen peroxide can be said to be an industrially advantageous method. However, there are only several examples that have been reported, in which hydrogen peroxide was used to subject a tetrasubstituted olefin compound to oxidative cleavage.
For example, Patent Documents 5 and 6 each disclose a method for producing ß-hydroxyhydroperoxides and ketones, the method being characterized by reacting tetrasubstituted olefin and hydrogen peroxide in the presence of a particular catalyst. The catalyst is at least one type of metal compound selected from the group consisting of tungsten metal, molybdenum metal, a tungsten compound composed of tungsten and a group IIIb element, a group IVb element, a group Vb element, or a group VIb element except oxygen, and a molybdenum compound composed of molybdenum and a group IIIb element, a group IVb element, a group Vb element, or a group VIb element except oxygen. Both Patent Documents describe that some reaction products cleave into diketones.